| Chicago to Santa Rosa (California) | 1,851.54 mi (2,979.77 km) |
| Chicago to Santaquin (Utah) | 1,261.33 mi (2,029.92 km) |
| Chicago to Santee (California) | 1,714.45 mi (2,759.15 km) |
| Chicago to Sapulpa (Oklahoma) | 605.02 mi (973.69 km) |
| Chicago to Saraland (Alabama) | 759.65 mi (1,222.55 km) |
| Chicago to Sarasota (Florida) | 1,043.08 mi (1,678.67 km) |
| Chicago to Sarasota Springs (Florida) | 1,046.16 mi (1,683.64 km) |
| Chicago to Saratoga (California) | 1,843.81 mi (2,967.33 km) |
| Chicago to Saratoga Springs (New York) | 713.32 mi (1,147.97 km) |
| Chicago to Saratoga Springs (Utah) | 1,261.67 mi (2,030.47 km) |
| Chicago to Sartell (Minnesota) | 417.72 mi (672.25 km) |
| Chicago to Satellite Beach (Florida) | 1,024.45 mi (1,648.69 km) |
| Chicago to Sauk Rapids (Minnesota) | 414.27 mi (666.70 km) |
| Chicago to Sault Ste. Marie (Michigan) | 360.41 mi (580.02 km) |
| Chicago to Savage (Minnesota) | 349.30 mi (562.15 km) |
